Stereoselective Synthesis of Tricyclo[6.2.2.0(2,7)]dodecane-3,6,9,10-tetrol via Selective Reduction of ,-Unsaturated 1,4-DIKetone

Abstract

Stereoselective synthesis of tricyclo[6.2.2.0(2,7)]dodecane-3,6,9,10-tetrol was developed starting from p-benzoquinone. The endo selective Diels-Alder cycloaddition of p-benzoquinone and 1,3-cyclohexadiene afforded the corresponding bicyclic diketone. The synthesis of the title compound was based on the cycloadduct by selective reduction with NaBH4, acetylation with AcCl, and hydroxylation with OsO4-NMO. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]